Total Synthesis of Norsampsones A and B, Garcinielliptones N and O, and Hyperscabrin A

Abstract

The asymmetric total synthesis of five decarbonyl polycyclic polyprenylated acylphloroglucinols norsampsnes A (3) and B (4), garcinielliptones O (5) and N (6), and hyperscabrin A (7) is described. The synthesis to construct the core substituted cyclohexanone ring of these natural products was achieved by a key Dieckmann condensation. The chirality of the molecules was introduced by the stereoselective alkylation with Evans' oxazolidinones. The synthesis could be run on grams scale, and the Dieckmann condensation was investigated through the DFT calculations to help improve the yield of garcinielliptone O (5). Determination of the absolute configuration of garcinielliptones O (5) and N (6) was also achieved.